In live music, there aren’t a lot of moves with a higher degree of difficulty than leaving your big hit single off the set list. And Ryan Bingham just stuck the landing. In November, at Holy Mountain—a small Austin club where he was kicking off a winter run of solo acoustic shows—Bingham’s best-known song,“The Weary Kind,” went unplayed. Perhaps more surprisingly, when he was taking requests, nobody shouted for the song, which he had co-written for the 2009 movie Crazy Heart. Not once. Maybe the crowd knew he’s played it sparingly—as in, almost never—since the song won him an Oscar, a Grammy, and a Golden Globe. For a few years, there were fans who felt cheated when he skipped the song. But that’s how Bingham thinned the herd and moderated expectations. As reassuring as it might be to have a song like that in your back pocket, if you’re not careful, people expect more songs like that. And that’s not the business Bingham signed up for. “I’m proud of ‘The Weary Kind,’ but I never felt like it was the best song I’d ever written,” says the 33-year-old. “I didn’t want to have to play it. I didn’t want to wind up defined by it.”

This March will mark five years since the night when Amanda Seyfried and Miley Cyrus handed Bingham that Oscar for Best Original Song. And while he hasn’t let that moment determine his identity, it’s only now that he’s truly come out the other side. His fifth album, Fear and Saturday Night, is the most hopeful and gracefully constructed set of songs he’s ever put out. It’s a far cry from the first album he wrote and recorded after “The Weary Kind” hit it big, 2012’s Tomorrowland, a jumble of loud but listless tunes he admits was something of a punk-rock move to test who was there for the statue and who was on board for real.

If Bingham’s best early work split the difference between folksy and fierce—think a young Steve Earle fronting the Allman Brothers—Tomorrowland was too chaotic, too bitter. Fear and Saturday Night, by contrast, is straightforward and tuneful, but also hardscrabble, which is pretty much Bingham’s sweet spot. If you suggest that it sounds like a return to the Ryan Bingham people thought they knew, he’ll go you one better. “Maybe it’s a return to the myself I thought I knew,” he says.

The reintroduction begins, helpfully enough, with “Nobody Knows My Trouble,” a song that builds his backstory verse by verse, from his birth in New Mexico to a childhood spread across a succession of small West Texas towns while his father chased oil-field labor. “Ever since I was a baby / I’ve been running from everything I know . . . nobody thought that I ever would get away with the trouble in me,” he sings. Then he gets to the heart of what marked and warped his early days: his parents’ raging alcoholism. “It didn’t take too long for the pills and the bottom of a bottle / to dig a deep grave with a shovel / and bury everything that a young boy needs.”

“I remember being not much more than a kid and having my grandma tell me she was surprised I wasn’t in prison,” says Bingham, who at twelve was already spending time in roadhouses with his father, shooting pool, drinking beer, and listening to Hank Williams and Bob Wills on the jukebox. “I hung with a tough crowd, but everybody I knew was tough. West Texas always felt a little hostile, like you had to learn to protect yourself early on. My parents were around, but I was really kind of on my own out there.”

When Bingham was a child, rodeos served as a lifeline. He hailed from a cattle-ranching family, and an uncle introduced him to junior rodeo; he rode steers at eleven and junior bulls at thirteen. It was more than a little dangerous, but by the time he was seventeen, he would need rodeo purses to put food on his plate. When his parents split up, he dropped out of school and got on the professional rodeo circuit. Unfortunately, he didn’t win often enough to pay the bills, so there were always day-labor gigs—digging ditches, building fences—between appearances. And before falling asleep in his car, he’d write songs on an acoustic guitar his mother had given him. Which is how a guy who didn’t have much interest in music found himself with a notebook full of songs—enough to eventually take a swing at a small open-mike night in Stephenville, where he walked away with more in tips than he’d made earlier that day building fences.

“When I made that first fifty dollars, I thought, ‘If I could do this three or four nights a week, what else could I need?’ ” he says. “It almost helped that I felt like I didn’t have any options. I didn’t have an education. I didn’t have family or friends that could get me a job. I was a broke kid on my own without a clue of where to begin. The guitar was freedom.”

Initially, Bingham played in small roadhouses and sports bars. Eventually, a regular circuit of gigs in San Antonio, New Braunfels, and Austin turned the Hill Country into the closest thing he had to home. Though that home, as it had for so long, sat on wheels. While he cut his teeth in Austin venues like the Continental Club and Momo’s, he lived in his truck behind fiddler Doug Moreland’s chain-saw-art gallery, in Manchaca. Both of his belongings fit in the truck: an acoustic guitar and a one-eyed blue heeler named Tasha, who could sit perfectly still on a bar stool while drunks balanced beer cans on her head. “She was a very talented dog,” Bingham says.

“Because of the rodeo trail, I knew how to travel light. It came naturally to live that way. It’s what I always knew growing up—living out of a suitcase and cardboard boxes, sleeping wherever you could lay your head down.”

A turning point came when some rudimentary demos he’d recorded in 2005 landed in the hands of West Texas singer-songwriter Terry Allen, who invited him to a party in Marfa, where he traded songs with the likes of Joe Ely, Butch Hancock, Guy Clark, and Robert Earl Keen. Ely was particularly impressed by Bingham’s songs and let him open some shows for him and sleep on his couch in Austin. Not long after, representatives from Lost Highway Records, a division of Universal Music Group Nashville, saw him open for Ely at Austin’s Cactus Cafe. He inked a deal with the label and put out two records—Mescalito and Roadhouse Sun—which earned strong reviews and sold decently.

But where exactly Bingham fit into the larger picture was a bit unclear. He admits he was never all that interested in running with the two scenes he could have most easily been grouped with: the rootsy Americana community that produced bona fide stars like Ryan Adams and Wilco or the Texas music movement that has meant big hometown money for folks like Pat Green and Jack Ingram. Instead, Bingham built a small, respectable fan base gig by gig and relied largely on word of mouth.

It was that word of mouth that led him to writer and director Scott Cooper, who’d been given a copy of Mescalito around the time he was casting a film about a down-on-his-luck country musician. Cooper took Bingham to lunch and offered him a bit part in the movie. He also asked him to write a song that the film’s star, Jeff Bridges, could sing. Bingham came back with “The Weary Kind,” which turned into the movie’s signature song.

But even after “The Weary Kind” swept the 2010 awards season and the album he released soon after, Junky Star, did well, Bingham began to realize that night after night of singing songs filled with weathered characters barely holding on was dragging him down. He’d always been a write-what-you-know songwriter who made no bones about treating music as therapy. But now the music felt less like therapy and more like depression itself.

“For a long time I was miserable, onstage and off,” says Bingham. “And you know what doesn’t pair well with depression? Not sleeping, eating poorly, and partying every night. I just stayed on the road tour after tour and wondered why I was always so sad.”

It seems obvious now, but it took years for Bingham to come around to the fact that at the core of his problems were the deaths of his parents. His mother passed in 2007, right around the time Mescalito was coming out. Then, not long after his big Oscar night, his father killed himself. Rather than deal with either of these losses, he just kept touring.

“My mother drank herself to death and my father shot himself,” says Bingham. “There are so many questions when your parents die like that. I never felt like my parents were bad people or didn’t love me, but it makes you wonder what it was they didn’t want to stick around for.”

Rather than just staying on the road and giving in to his despair, Bingham sought professional help a few years ago. He talked a lot about his parents and his strange childhood and the loneliness of life on the road, all of which was important. But the great realization was that his vocation was also his salvation. “It took taking off to realize it wasn’t the music that bummed me out,” he says. “It was the music that was keeping me alive.” To mark the clean slate, Bingham wrote most of Fear and Saturday Night during a few weeks of isolation while living in an Airstream in California’s Santa Monica Mountains. If there’s one clear takeaway from Bingham’s story, it’s that he does some of his best work sitting alone in a vehicle with his guitar.

None of which means that Bingham is poised for some kind of breakthrough, or that he wants one. His career started with nothing to go back to, nothing to lose, and that’s where it’s stayed. Unlike most singer-songwriters, who see their craft as the embodiment of a lifelong dream, Bingham got into it as a job that paid better and chapped his ass less than digging ditches and riding bulls. And there’s a sort of freedom in that too. He’s content living from one record and one tour to the next, because what’s the alternative? Some of that zen he got from therapy. The rest he got from Texas’s original zen master, Willie Nelson.

“I learned a lot when I toured with Willie a couple years ago,” he says. “One night we played a big outdoor show in Portland to, like, twenty thousand people. The next night, we were in some dirty casino in Reno. The first three rows were elderly folks with oxygen tanks, clutching buckets of pennies to play the slots. It was one extreme to the other. But he’s Willie Nelson. This is it. If you’re going to play music for the rest of your life, this is it. You have to ask yourself, ‘Do you know what’s important to you about the music? Are you going to do this for life?’ Two years ago, I don’t know if I had the answers. But now, the answer is yes, all of the above. I don’t have any hesitation or doubt anymore.”

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